The role of electronice effects in determining aldol diastereoselection is investigated, by electronic perturbation of both the aldehyde and arylacetonitrile components. Secondly, a preliminary investigation of the aldol stereoselectivity of aliphatic nitriles is described. Finally, we demonstrate the transformation of β-hydroxy nitriles to a variety of diastereomerically pure and highly functionalized acyclic and heterocyclic γ-amino alcohol derivatives.

Key words: STEREOSELECTIVITY, NITRILE, AROMATIC ALDEHYDE, ELECTRONIC STRUCTURE